Diisopropylethylamine → HCID 89816135, compound

HRID 1483010Notes

Reaction equation

HRID 1483010 reaction equation
[CH:1]([CH:4]1[C:9]2=[CH:10][C:11]3[CH:12]=[CH:13][C:14]([S:17][CH3:18])=[CH:15][C:16]=3[N:8]2[CH2:7][CH2:6][NH:5]1)([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.Cl[C:29]1[N:34]=[C:33]([C:35]([F:38])([F:37])[F:36])[C:32]([C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:31][N:30]=1>CC(O)C>[CH:1]([CH:4]1[C:9]2=[CH:10][C:11]3[CH:12]=[CH:13][C:14]([S:17][CH3:18])=[CH:15][C:16]=3[N:8]2[CH2:7][CH2:6][N:5]1[C:29]1[N:34]=[C:33]([C:35]([F:37])([F:38])[F:36])[C:32]([C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:31][N:30]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2780355Ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylateHCID 89816011HCID 89816011, compound

Product 1

HCID 89816135HCID 89816135, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 1-isopropyl-7-(methylthio)-1,2,3,4-tetrahydropyrazino[1,2-a]indole (100 mg, 0.38 mmol) and DIPEA (248.3 mg, 1.921 mmol) in i-PrOH (3 mL) was added ethyl 2-chloro-4-(trifluoromethyl)pyrimidine-5-carboxylate (196 mg, 0.77 mmol). The reaction mixture was stirred at rt overnight. The mixture was concentrated and purified by preparative TLC on silica gel eluting with PE/EtOAc 1:1 to afford ethyl 2-(1-isopropyl-7-(methylthio)-3,4-dihydropyrazino[1,2-a]indol-2(1H)-yl)-4-(trifluoromethyl)pyrimidine-5-carboxylate (60 mg, 32.6% yield) as a colorless oil. LC-MS MS (ESI) m/z 478.7 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by preparative TLC on silica gel eluting with PE/EtOAc 1:1

Sources & evidence

ORD record
ord-015f8d9b714e4f3294ebc0851cc6d195
Source dataset
uspto-grants-2016_08
Patent number
US09416135B2

Reaction notes

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